Preparation of anthraquinone imide compounds

Abstract

The preparation of anthraquinone imide compounds by condensation of anthraquinone compounds containing at least one primary amino group with halogenized aromatics or by condensation of halogenized anthraquinone compounds with primary aromatic amines, in the presence of a vat-dyeing catalyst and an acid-binding agent in an organic solvent, in which the organic solvent used is an alkyl benzoate.

We claim: 
     
       1. A process for the preparation of an anthraquinone imide compound, comprising condensation of an anthraquinone compound containing at least one primary amino group with a halogenized aromatic compound or by condensation of a halogenized anthraquinone compound with a primary aromatic amine, in the presence of a vat-dyeing catalyst and an acid-binding agent in an organic solvent, wherein the organic solvent used is an alkyl benzoate. 
     
     
       2. A process as defined in claim 1, wherein the organic solvent used is methyl benzoate. 
     
     
       3. A process as defined in claim 1 further comprising conducting said condensation in the presence of an oxidizing agent. 
     
     
       4. The process of claim 1, wherein said anthraquinone imide compound is of the formula I wherein R is phenyl, anthraquinone, benzanthrone, anthanthrone, pyranthrone, dibenzanthrone, isodibenzanthrone, anthraquinone acridone, flavanthrone, fluoroanthene, dibenzpyrenequinone or a condensation product thereof,   each of which may be optionally substituted with a halogen, hydroxy, C 1  -C 4  alkyl, amino, C 1  -C 4  alkylamino, C 1  -C 4  alkynoylamino, benzoylamino, or benzoylamino substituted with halogen or C 1  -C 4  alkyl,   X is halogen, hydroxy, C 1  -C 4  alkyl, amino, C 1  -C 4  alkylamino, C 1  -C 4  alkanoylamino, benzoylamino, or benzoylamino substituted with halogen or C 1  -C 4  alkyl,   m is an integer from 1 to 4, and   n is an integer from 1 to 4.